Cyclic hydropyran oligolides as preorganized ligand arrays: Modular assembly of 18-, 24-, 36-, 48-, 54- and 72-membered rings via iteration and cyclooligomerization

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 343-346

  Burke, Steven D ^a   Heap, Charles R ^a   Porter, Warren J ^b   Song, Yuntao ^c  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; PYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030050873     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02168-X     Document Type: Article

References (27)

1. (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020.
2. (b) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436.
3. (c) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1991, 91, 1721-2085.
4. (d) Kilburn, J. D.; Patel, H. K. Contemporary Organic Synthesis 1994,1, 259-286.
5. (a) Vogtle, F.; Weber, E. Host Guest Complex Chemistry: Macrocycles: Synthesis, Structures, Applications; Vogtle, F.; Weber, E., Ed.; Springer: Berlin, 1985.
6. (b) Dean, P. M. Molecular Foundation of Drug-Receptor Interaction; Cambridge University Press: Cambridge, 1987.
7. Mascal, M. Contemporary Organic Synthesis 1994, 1, 31-46.
8. (a) Burke, S. D.; Porter, W. J.; Rancourt, J.; Kaltenbach, R. F. Tetrahedron Lett. 1990, 31, 5285-5288.
9. (b) Burke, S.D.; O'Donnell, C.J.; Porter, W.J; Song, Y. J. Am. Chem. Soc. (in press).
10. 2-.
11. Burke, S. D.; Armistead, D. M.; Schoenen, F. J.; Fevig, J. M. Tetrahedron 1986, 42, 2787-2801.
12. Burke, S. D.; Deaton, D. N.; Olsen, R. J.; Armistead, D. M.; Blough, B. E. Tetrahedron Lett. 1987, 28, 3905-3906.
13. Modules 17 and 19 and the derived macrocycles 1, 3, 6, and 8 were actually prepared in the other enantiomeric series, consistent with starting esters 14 and 15.
14. The structural and functional distinctions that result between diastereomers 1 and 2, 3 and 4, 5 and 6, and 7 and 8 are discussed in ref. 4b.
15. (a) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
16. (b) Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522-524.
17. (c) Hassner, A.; Krepski, L. R.; Alexanian, V. Tetrahedron 1978, 34, 2069-2076.
18. Lipshutz, B. H.; Pegram, J. J.; Morey, M. C. Tetrahedron Lett. 1981, 22, 4603-4606.
19. (a) Woodward, R. B.; Heusler, K.; Gosteli, J.; Naegeli, P.; Oppolzer, W.; Ramage, R.; Ranganathan, S.; Vorbrüggen, H. J. Am. Chem. Soc. 1966, 88, 852-853.
20. b) Just, G.; Grozinger, K. Synthesis 1976, 457-458.
21. Properties of the hexahydro analogues 3, 4, 7, and 8 mirrored those of their respective parents 1, 2, 5, and 6. Alternative transformations of the alkene moieties will be reported elsewhere.
22. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
23. Because of constitutional symmetry and conformational flexibility in solution, the NMR spectra of 2, 9, 10, 11, 12, and 13 are not mutually distinctive. Structural assignments of these macrocycles, readily separable by silica gel chromatography, are based upon crystallographic and/or FAB (liquid SIMS) mass spectrometric analyses.
24. For observations regarding cyclooligomerization of (R)-3-hydroxybutanoic acid via the Yamaguchi protocol, see: Seebach, D.; Brändli, U.; Schnurrenberger, P.; Przybylski, M. Helv. Chim. Acta 1988, 71, 155-167.
25. (a) For "modified" Yamaguchi lactonization conditions, see: Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. J. Org. Chem. 1990, 55, 7-9.
26. (b) For a related temperature dependence in monomer versus dimer formation, see: Hammond, P. J.; Beer, P. D.; Hall, C. D. J. Chem. Soc., Chem. Commun. 1983, 1161-1163.
27. These large cyclic oligomers do not interconvert under the reaction conditions, suggesting that their formation is a kinetically-controlled process.